A metal catalyst-free and one-pot synthesis of (3,4-dihydro-2H-benzo[b][1,4]oxazin-2-yl)methanol derivatives in water

被引:4
作者
Singh, Shambhu Nath [1 ,2 ,3 ]
Jayaprakash, Sarva [1 ,2 ]
Reddy, K. Venkateshwara [3 ,4 ]
Nakhi, Ali [5 ]
Pal, Manojit [5 ]
机构
[1] Custom Pharmaceut Serv, Hyderabad 500049, Andhra Pradesh, India
[2] Dr Reddys Labs Ltd, Hyderabad 500049, Andhra Pradesh, India
[3] JNT Univ, JNTUH Coll Engn, Dept Chem, Hyderabad 500085, Andhra Pradesh, India
[4] JNTU, CMR Engn Coll, Hyderabad 501401, Andhra Pradesh, India
[5] Dr Reddys Inst Life Sci, Hyderabad 500046, Andhra Pradesh, India
来源
RSC ADVANCES | 2015年 / 5卷 / 103期
关键词
3,4-DIHYDRO-2H-1,4-BENZOXAZINE DERIVATIVES; ANTITHROMBOTIC COMPOUNDS; DUAL FUNCTION; RECEPTOR; ANTAGONISTS; CHEMISTRY; DISCOVERY;
D O I
10.1039/c5ra14478g
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A robust and metal catalyst-free method has been developed for the general and green synthesis of racemic (3,4-dihydro-2H-benzo[b][1,4] oxazin-2-yl)methanol derivatives. This simple, mild and practical method involves the reaction of 2-aminophenols with (+/-)-epichlorohydrin in the presence of NaOH in water at room temperature. The reaction features high regioselectivity and a good substrate scope to produce both N-substituted and N-unsubstituted products.
引用
收藏
页码:84889 / 84893
页数:5
相关论文
共 50 条
  • [41] Facile one-pot multicomponent synthesis of 1H-pyrazolo[3,4-b]quinolines using L-proline as a catalyst
    Hegde, Hemant
    Shetty, Nitinkumar S.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2017, 53 (08) : 883 - 886
  • [42] One-pot synthesis of 6H-benzo[b]benzo[4,5]imidazo[1,2-d][1,4]oxazines via a copper-catalyzed process
    Huang, Aiping
    Liu, Huanhuan
    Ma, Chen
    RSC ADVANCES, 2013, 3 (33): : 13976 - 13982
  • [43] 1,3-Dihydro-benzo[b][1,4]Diazepin-2-one Derivatives as Potent Non-Competitive Metabotropic Glutamate Receptor 2/3 Antagonists
    Woltering, T. J.
    Wichmann, J.
    Goetschi, E.
    Huwyler, J.
    Knoflach, F.
    Ballard, T. M.
    Gatti, S.
    CURRENT NEUROPHARMACOLOGY, 2011, 9 : 67 - 67
  • [44] α-Zirconium Sulfophenylphosphonate as a Catalyst for the Synthesis of 3,4-Dihydropyrimidin-2(1H)-One Derivatives Under Solvent Free Conditions
    Rosati, Ornelio
    Curini, Massimo
    Montanari, Francesca
    Nocchetti, Morena
    Genovese, Salvatore
    CATALYSIS LETTERS, 2011, 141 (06) : 850 - 853
  • [45] Four-component catalyst-free reaction in water: Combinatorial library synthesis of novel 2-amino-4-(5-hydroxy-3-methyl-1H-pyrazol-4-yl)-4H-chromene-3-carbonitrile derivatives
    Kumaravel, Kandhasamy
    Vasuki, Gnanasambandam
    GREEN CHEMISTRY, 2009, 11 (12) : 1945 - 1947
  • [46] Catalyst-free, one-pot three-component synthesis of N,3-diphenybenzo[d]imidazo[2,1-b]thiazoles and oxybis(1-phenyl-2-(phenylamino)ethanones)
    Hajipour, Mina
    Mehrabi, Hossein
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2023, 60 (05) : 879 - 888
  • [47] Efficient catalyst-free tricomponent synthesis of new spiro[cyclohexane-1,4′-pyrazolo[3,4-e][1,4]thiazepin]-7′(6′H)-ones
    Becerra-Rivas, Christian
    Cuervo-Prado, Paola
    Orozco-Lopez, Fabian
    SYNTHETIC COMMUNICATIONS, 2019, 49 (03) : 367 - 376
  • [48] One-Pot Multicomponent Solvent-Free Synthesis of 2-Amino-4H-benzo[b]pyrans Catalyzed by Per-6-amino-β-cyclodextrin
    Azath, Ismail Abulkalam
    Puthiaraj, Pillaiyar
    Pitchumani, Kasi
    ACS SUSTAINABLE CHEMISTRY & ENGINEERING, 2013, 1 (01): : 174 - 179
  • [49] NOVEL ONE-POT MULTICOMPONENT SYNTHESIS OF SUBSTITUTED 2,3-DIHYDRO-2-(6-(4-HYDROXY-6-METHYL-2-OXO-2H-PYRAN-3-YL)-7H-[1,2,4] TRIAZOLO[3,4-b][1,3,4] THIADIAZIN-3-YL) PHTHALAZINE-1,4-DIONES AND SUBSTITUTED 3-[3-(N'-BENZYLIDENE-HYDRAZINO)-7H-[1,2,4] TRIAZOLO[3,4-b][1,3,4] THIADIAZIN-6-YL]-4-HYDROXY-6-METHYL-PYRAN-2-ONES
    Thirupaiah, Bade
    Vedula, Rajeswar Rao
    SYNTHETIC COMMUNICATIONS, 2014, 44 (04) : 513 - 519
  • [50] Potential antimicrobial agents from triazole-functionalized 2H-benzo[b] [1,4]oxazin-3(4H)-ones
    Bollu, Rajitha
    Banu, Saleha
    Bantu, Rajashaker
    Reddy, A. Gopi
    Nagarapu, Lingaiah
    Sirisha, K.
    Kumar, C. Ganesh
    Gunda, Shravan Kumar
    Shaik, Kamal
    BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2017, 27 (23) : 5158 - 5162